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Private Beach
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Oceanfront
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Breakfast
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EV Charge Station

Discover the Best Resort Vacations
Explore the top resorts, from luxury beachfront escapes to family-friendly all-inclusive resorts and relaxing spa retreats. Whether you’re planning a weekend getaway or an extended vacation, the Madison offers world-class resort destinations for every travel style, season, and budget.
Guests
- Hotels
- Villas
- Cabins
- Rentals
- Cottages
- Resorts
- Accommodations
- Old Saybrook
- ·
- Madison Center
- 0.66 mi to center
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
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Oceanfront
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Parking
-
Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison
- 4.77 mi to center
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
- Old Saybrook
- ·
- Madison Center
- 0.76 mi to center
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
- Old Saybrook
- ·
- Madison
- 4.46 mi to center
-
Oceanfront
-
Parking
-
Ocean View
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Balcony/Terrace
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Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison Center
- 0.68 mi to center
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Private Pool
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Oceanfront
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Parking
-
Pool
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Private Pool
-
Oceanfront
-
Parking
-
Pool
- Old Saybrook
- ·
- Madison Center
- 0.67 mi to center
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Parking
-
Ocean View
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Balcony/Terrace
-
View
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Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison
- 4.16 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison
- 4.32 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Old Saybrook
- ·
- Madison Center
- 0.66 mi to center
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison
- 4.77 mi to center
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
- Old Saybrook
- ·
- Madison Center
- 0.76 mi to center
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
- Old Saybrook
- ·
- Madison
- 4.46 mi to center
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison Center
- 0.68 mi to center
-
Private Pool
-
Oceanfront
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Parking
-
Pool
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
- Old Saybrook
- ·
- Madison Center
- 0.67 mi to center
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison
- 4.16 mi to center
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison
- 4.32 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Old Saybrook
- ·
- Madison Center
- 0.66 mi to center
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison
- 4.77 mi to center
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
- Old Saybrook
- ·
- Madison Center
- 0.76 mi to center
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
- Old Saybrook
- ·
- Madison
- 4.46 mi to center
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison Center
- 0.68 mi to center
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
- Old Saybrook
- ·
- Madison Center
- 0.67 mi to center
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison
- 4.16 mi to center
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison
- 4.32 mi to center
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Parking
-
Balcony/Terrace
-
Kitchen
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Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Old Saybrook
- ·
- Madison Center
- 0.66 mi to center
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison Center
- 0.58 mi to center
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Parking
-
Internet
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Security/Safety
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Guest Services
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Parking
-
Internet
-
Security/Safety
-
Guest Services
- Old Saybrook
- ·
- Madison
- 4.10 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
-
View
-
Kitchen
- Old Saybrook
- ·
- Madison
- 3.97 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison
- 4.45 mi to center
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
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Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison
- 4.26 mi to center
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
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Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison
- 4.17 mi to center
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Hot Tub
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Parking
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Ocean View
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Balcony/Terrace
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Hot Tub
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Parking
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Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison
- 1.90 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
-
View
-
Kitchen
- Old Saybrook
- ·
- Madison Center
- 0.66 mi to center
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison
- 4.77 mi to center
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
- Old Saybrook
- ·
- Madison Center
- 0.76 mi to center
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
- Old Saybrook
- ·
- Madison
- 4.46 mi to center
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison Center
- 0.68 mi to center
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
- Old Saybrook
- ·
- Madison Center
- 0.67 mi to center
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison
- 4.16 mi to center
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Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison
- 4.32 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Old Saybrook
- ·
- Madison
- 2.91 mi to center
-
Private Pool
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Private Pool
-
Pool
-
Balcony/Terrace
-
Kitchen
Find the Perfect Resort Vacation in the Madison
What makes our resorts stand out?
Verified Properties
Every vacation home shown on Resort Vacation comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Popular Resort Destinations in the Madison
What are the Top Resort Locations Across the Madison?
Discover resorts in the most sought-after travel destinations nationwide:
Hammonasset Beach State Park
Hammonasset Beach State Park VACATION RENTALSHammonasset Beach
Hammonasset Beach VACATION RENTALSMeigs Point Nature Center
Meigs Point Nature Center VACATION RENTALSMadison Center
Madison Center VACATION RENTALSDeacon John Grave House
Deacon John Grave House VACATION RENTALSNorth Madison Shopping Center
North Madison Shopping Center VACATION RENTALSAnna Mia's
Anna Mia's VACATION RENTALSRJ Julia Booksellers
RJ Julia Booksellers VACATION RENTALSScranton Memorial Library
Scranton Memorial Library VACATION RENTALSAllis-Bushnell House and Museum
Allis-Bushnell House and Museum VACATION RENTALSHow to Reserve Your Resorts Vacation Accommodation?
Booking Made Simple
Resorts Vacations connects travelers with verified resort stays from trusted partners across the Madison. Once you find the perfect resort, you’ll be seamlessly guided to our partner’s secure booking platform to complete your reservation with confidence.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Common Resort Vacation Amenities in the Madison
What Amenities Can You Expect When Booking with Resorts Vacations?
Resorts Vacations offers carefully selected resort stays across the Madison, designed for comfort, convenience, and memorable experiences.
Indoor Amenities
Spacious guest rooms and suites
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Places to Stay with Resorts Vacations
Looking for the perfect resort vacation in the Madison? Discover a curated collection of resort stays offering comfort, convenience, and unforgettable experiences in top destinations nationwide. Whether you’re searching for a beachfront resort, a family-friendly escape, or a luxury retreat, Resorts Vacations makes it easy to explore and compare verified resort options for your next getaway.
- Old Saybrook
- ·
- Madison Center
- 0.76 mi to center
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
- Old Saybrook
- ·
- Madison Center
- 0.66 mi to center
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison
- 2.25 mi to center
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison
- 4.46 mi to center
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison Center
- 0.68 mi to center
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
- Old Saybrook
- ·
- Madison
- 4.83 mi to center
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Parking
-
Ocean View
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Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison Center
- 0.67 mi to center
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison Center
- 0.69 mi to center
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Parking
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Ocean View
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Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison
- 4.16 mi to center
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Parking
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Ocean View
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Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison
- 3.78 mi to center
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Parking
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Ocean View
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Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison
- 4.52 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Old Saybrook
- ·
- Madison
- 4.26 mi to center
-
Oceanfront
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Parking
-
Ocean View
-
Balcony/Terrace
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
Resorts Vacations FAQs
Which vacation homes in Madison are best for families?
If you are looking for a family-friendly vacation home in Madison, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Madison:
How many vacation rentals are available in Madison?
Currently, the total number of properties listed in 2026 is over 92 in the Madison area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Madison.
More Resorts Vacations to Explore
- Old Saybrook
- ·
- Madison Center
- 0.58 mi to center
-
Parking
-
Ocean View
-
View
-
Kitchen
-
Parking
-
Ocean View
-
View
-
Kitchen
- Old Saybrook
- ·
- Madison Center
- 0.58 mi to center
-
Parking
-
Internet
-
Security/Safety
-
Guest Services
-
Parking
-
Internet
-
Security/Safety
-
Guest Services
- Old Saybrook
- ·
- Madison
- 2.25 mi to center
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison Center
- 0.76 mi to center
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
- Old Saybrook
- ·
- Madison
- 4.77 mi to center
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
- Old Saybrook
- ·
- Madison Center
- 0.89 mi to center
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Parking
-
Balcony/Terrace
-
View
-
Kitchen
-
Parking
-
Balcony/Terrace
-
View
-
Kitchen
- Old Saybrook
- ·
- Madison
- 4.10 mi to center
-
Parking
-
Balcony/Terrace
-
View
-
Kitchen
-
Parking
-
Balcony/Terrace
-
View
-
Kitchen
- Old Saybrook
- ·
- Madison Center
- 0.76 mi to center
-
Breakfast
-
EV Charge Station
-
Parking
-
Balcony/Terrace
-
Breakfast
-
EV Charge Station
-
Parking
-
Balcony/Terrace
- Old Saybrook
- ·
- Madison
- 4.83 mi to center
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Old Saybrook
- ·
- Madison Center
- 0.71 mi to center
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Old Saybrook
- ·
- Madison
- 4.67 mi to center
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Parking
-
Kitchen
-
Air Conditioner
-
Internet
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
- Old Saybrook
- ·
- Madison Center
- 0.35 mi to center
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Parking
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Balcony/Terrace
-
View
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
View
-
Air Conditioner